Yan Yangwen, Geng Wang, Chen Chao, Yan Kai, Gan Xiuhai
State Key Laboratory of Green Pesticide, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Guiyang 550025, China.
School of Biological Science and Technology, Liupanshui Normal University, Liupanshui 553004, China.
J Agric Food Chem. 2025 Sep 10;73(36):22150-22161. doi: 10.1021/acs.jafc.5c02008. Epub 2025 Aug 27.
Protoporphyrinogen IX oxidase (PPO) is an essential enzyme in the chlorophyll synthesis process in plants, making it a major target for the advancement of environmentally safe herbicides. In order to develop new PPO inhibition herbicides, a series of novel pyrazole derivatives containing carbonic ester moieties were synthesized based on the active splicing principle and structural simplification strategy. In bioassays, it was found that the majority of the target compounds had a good inhibitory effect on PPO (PPO) and displayed herbicidal activity against the tested weeds. Among them, compound ( = 15.2 nM) not only exhibited an inhibitory effect on PPO superior to that of pyraflufen-ethyl ( = 31.1 nM) and fluazolate ( = 18.3 nM) but also showed more than 90% herbicidal activity against dicotyledonous weeds at 9.375 g of a.i./ha, and its herbicidal activity was better than that of pyraflufen-ethyl and fluazolate. Additionally, compound caused lower damage to wheat, rice, corn, soybeans, peanuts, and cotton compared to pyraflufen-ethyl and fluazolate. Molecular docking revealed that there are two hydrogen bonds between compound and the Arg98 (2.8 and 3.0 Å) residue of PPO, which were stronger than those of pyraflufen-ethyl (2.9 Å) and fluazolate (2.9 and 3.6 Å). Density functional theory calculations clarified the differences of the target compounds in herbicidal activity. The current study suggests that compound shows potential as a PPO inhibitor for creating an ecofriendly herbicide to manage weeds in agricultural fields.
原卟啉原IX氧化酶（PPO）是植物叶绿素合成过程中的一种关键酶，这使其成为开发环境安全型除草剂的主要靶点。为了研发新型PPO抑制型除草剂，基于活性拼接原理和结构简化策略，合成了一系列含有碳酸酯基团的新型吡唑衍生物。在生物测定中发现，大多数目标化合物对PPO具有良好的抑制作用，并对受试杂草表现出除草活性。其中，化合物（IC₅₀ = 15.2 nM）不仅对PPO的抑制作用优于乙羧氟草醚（IC₅₀ = 31.1 nM）和唑酮草酯（IC₅₀ = 18.3 nM），而且在9.375 g a.i./ha剂量下对双子叶杂草的除草活性超过90%，其除草活性优于乙羧氟草醚和唑酮草酯。此外，与乙羧氟草醚和唑酮草酯相比，化合物对小麦、水稻、玉米、大豆、花生和棉花的损害更低。分子对接显示，化合物与PPO的Arg98残基（2.8和3.0 Å）之间存在两个氢键，比乙羧氟草醚（2.9 Å）和唑酮草酯（2.9和3.6 Å）的氢键更强。密度泛函理论计算阐明了目标化合物在除草活性方面的差异。当前研究表明，化合物作为一种PPO抑制剂具有潜力，可用于创制一种生态友好型除草剂来治理农田杂草。
